20 Outfits That Make the '90s Look the Coolest

Avery Matera
·4 min read

The ’90s are back with a fervor. With trends first coming back onto the fashion scene a few seasons ago, we’ve truly hit our stride as we learn new and interesting ways to mix the retro trends into our more modern wardrobes. Without looking like we’re straight out of a Spice Girls music video or an Adidas advertisement from 1995, we’ve developed a huge crush on the style favorites that made the decade what it was. Our wardrobes are now rife with crop tops, track pants, and bomber jackets, and our after-hours looks consist of slip dresses, platform heels, and the occasional tube top. That’s right: We’ve reached peak ’90s nostalgia, but we’ve added an updated twist.

Taking a retro trend and running with it isn’t always easy, though, so we’re looking for inspiration from some of our favorite street style stars and fashion lovers alike. They’re styling bralettes under suiting, mixing crop tops with high-waisted midi skirts, and tapping into childhood nostalgia with vintage tees and cutoff jean shorts. And don’t even get us started on our collection of high-waisted jeans and chunky sneakers. Pure casual-cool. With these looks, though, nothing has ever been simpler to craft. Scroll through our favorite easy ’90s outfits below and you’ll be dressing as the better version of your childhood self in no time.

Slip Dress + Sneakers

The boudoir trend is alive and well in the slip dress, but it’s made more daytime-friendly with the addition of sneakers. Throw on a leather jacket if you’re looking to cover up a little more while you’re on the go.

Urban Outfitters Mallory Cowl Neck Slip Dress ($49)

Vans Old Skool Sneaker ($60)

Slip Dress + Tee

Turn your after-hours slip dress into a daytime-friendly look with a graphic tee underneath.

Bardot Mini Cami Slip Dress in Black ($24)

Year of Ours Joy Baby Tee ($59)

Bomber Jacket + Jeans

With jeans and a T-shirt as your base, play with ’90s accessories and layers, like the addition of a bomber jacket or colorful sunglasses.

H&M Satin Bomber Jacket ($50)

Ray-Ban Rb3447 Phantos Round Sunglasses ($154)

Madewell The Perfect Vintage Jeans ($120)

Overalls + Converse

Make sure to have plenty of overalls on hand, but don’t think you have to wear them exactly like everyone else. Fashion a one-shoulder or folded-down look by playing with the straps in new and interesting ways.

H&M Denim Overalls ($50)

Converse Chuck Taylor Low Top Sneaker ($50)

Trench Coat + Loose Jeans

Loose jeans, especially distressed pairs, feel just as ’90s as they do now. Make the look tailored with the addition of a trench coat.

Mango Lyocell Flowy Trench ($130)

Agolde '90s Fit Mid Rise Loose Fit Jeans ($188)

Overalls + Plaid Shirt + Combat Boots

Throw together all your favorite ’90s trends with a sleeveless turtleneck, overalls, a plaid button-down, and combat boots. We’ve officially reached peak retro.

BDG Baggy Denim Overall ($99)

Dr. Martens 1460 Pascal Virginia 8 Eye Boots ($150)

Floral Dress + Sneakers

There’s nothing better than an ultra-flirty ruffle, especially in a summery tone of yellow. Dress down the cocktail-ready look with a pair of low-top sneakers or casual sandals this summer.

Faithfull the Brand Le Galet Paisley-Print Crepe Midi Dress ($229)

Nike Air Force 1 Sage Low Platform Sneaker ($100)

Micro-Floral Dress + Tube Socks + Sneakers

Add an extra layer to your favorite LBD by throwing on a graphic tee underneath. Top the whole look with a leather jacket and finish it off with your favorite pair of low-top sneakers.

Reformation Lillet Dress ($218)

Nike Performance Cushion Crew Socks ($25)

Reebok Club C Double Sneakers ($80)

Minidress + Bomber Jacket + Booties

A bomber jacket is an easy retro go-to when you’re looking for a way to make your all-black look a little more retro.

Mango Pockets Linen Jacket ($120)

Eloquii Scoop Neck Dress ($100)

Overalls + Crop Top

Throw your most authentic baby tee underneath a pair of overalls to channel your most beloved childhood look in a more adult way.

We the Free Ziggy Denim Overalls ($98)

Intimately Be Alright Crop ($38)

Next, 30 Fashion Items That Look Like They're Straight Out of a '90s Catalog

This post was published at an earlier date and has been updated.

This article originally appeared on Who What Wear

Read More from Who What Wear